Drew Houston

5 statements across 2 episodes · 3 bullish · 1 bearish · 2 people on the record · first statement Oct 23, 2025 by Drew Houston · said 3 times in 2 episodes since 2024 · across every show →

On the record as a speaker too: Drew Houston's record, appearances and statements → this page counts the times other people say the name.

Mentions by year

brought up most by Travis Kalanick (2), John Coogan (1)

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2026 2 mentions in 1 episode

FULL INTERVIEW: Uber Founder Travis Kalanick is Back with a New AI Startup Mar 13, 2026 · 2 mentions · from 22:39
every mention in 2026, scene by scene →

2024 1 mention in 1 episode

The Secret Billionaire Party (ep6) Nov 3, 2024 · 1 mention · from 1:13:19
every mention in 2024, scene by scene →

every mention, scene by scene, with the transcript →

Everything said about Drew Houston, oldest first

Oct 23, 2025 negative

Disclosure

Houston: Dropbox draws a hard line against adopting advertising

“We're just going to draw a hard line. We're never, we're just not going to do that. Because of this trust conflict or this incentive conflict we would have.”

Drew Houston Oct 23, 2025 ▶ 11:53 Are AI Agents Further Away Than We Think? | Dropbox CEO Drew Houston Joins TBPN

Oct 23, 2025 positive

Assertion Supported

Houston: Dropbox reaches 500k paying businesses and $2.5B in revenue

“We have half a million paying businesses on Dropbox, two and a half billion in revenue.”

Drew Houston Oct 23, 2025 ▶ 18:20 Are AI Agents Further Away Than We Think? | Dropbox CEO Drew Houston Joins TBPN

Oct 23, 2025 positive

Assertion Supported

Houston: Dash avoids the six-month, $50K setup of competitors like Glean

“Well, and then I think that the big thing our customers really want or where Dash fits in there versus Glean or some other companies is like, you don't have to spend six months and 50 grand to get started.”

Drew Houston Oct 23, 2025 ▶ 20:44 Are AI Agents Further Away Than We Think? | Dropbox CEO Drew Houston Joins TBPN

Oct 23, 2025 neutral

Insight

Houston: At million-user scale, 99% reliability means thousands of daily failures

“Once you get up to a million users, even if you have a 95 or 99% success rate, that's still, like, thousands or 10,010 of thousands of people having, like, a really terrible experience, like, every day.”

Drew Houston Oct 23, 2025 ▶ 7:40 Are AI Agents Further Away Than We Think? | Dropbox CEO Drew Houston Joins TBPN

Mar 13, 2026 positive

Assertion Contradicted

Drew Houston Pioneered Late-Stage Institutional Fundraising for Tech Startups

“I have to give credit to Drew at Dropbox. He was like the first guy in that game.”

Travis Kalanick Mar 13, 2026 ▶ 22:39 FULL INTERVIEW: Uber Founder Travis Kalanick is Back with a New AI Startup

Drew Houston

Mentions by year

Everything said about Drew Houston, oldest first

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